Insights from recent episode analysis
Audience Interest
Podcast Focus
Publishing Consistency
Platform Reach
Insights are generated by CastFox AI using publicly available data, episode content, and proprietary models.
Most discussed topics
Brands & references
Est. Listeners
Insufficient chart data. Estimates will improve as the show charts.
- Per-Episode Audience
Est. listeners per new episode within ~30 days
N/A🎙 Weekly cadence·60 episodes·Last published 4mo ago - Monthly Reach
Unique listeners across all episodes (30 days)
N/A - Active Followers
Loyal subscribers who consistently listen
N/A
Market Insights
Platform Distribution
Reach across major podcast platforms, updated hourly
Total Followers
—
Total Plays
—
Total Reviews
—
* Data sourced directly from platform APIs and aggregated hourly across all major podcast directories.
On the show
From 10 epsHost
Recent guests
Recent episodes
Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success
Feb 11, 2026
1h 12m 47s
Omar Haroun: “Outsized Impact is Incredibly Rewarding”
Jan 8, 2026
1h 00m 55s
The Wealth Lag: What Happens AFTER Financial Freedom
Dec 9, 2025
14m 30s
Daniel Kivatinos Post-Exit: Why I Am Building Again
Nov 21, 2025
57m 55s
Justin Donald: The Post‑Wealth Work‑Life Balance
Oct 30, 2025
1h 00m 18s
Social Links & Contact
Official channels & resources
Official Website
Login
RSS Feed
Login
Resolving iTunes ID\u2026 if this persists, the podcast may not be indexed on Apple Podcasts.
| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 2/11/26 |  Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success✨ | post-wealth apathyfinancial success+4 | — | Exit Paradox | — | financial freedomcomfort optimization+5 | — | 1h 12m 47s | |
| 1/8/26 |  Omar Haroun: “Outsized Impact is Incredibly Rewarding”✨ | emotional cost of successidentity collapse+5 | Omar Haroun | — | — | entrepreneurshipidentity collapse+7 | — | 1h 00m 55s | |
| 12/9/25 |  The Wealth Lag: What Happens AFTER Financial Freedom✨ | financial freedomWealth Lag+4 | — | — | — | Wealth Lagfinancial freedom+5 | — | 14m 30s | |
| 11/21/25 |  Daniel Kivatinos Post-Exit: Why I Am Building Again✨ | post-exit storiesentrepreneurship+3 | Daniel Kivatinos | DrChronoJustPaid+1 | Silicon Valley | post-exitentrepreneur+3 | — | 57m 55s | |
| 10/30/25 |  Justin Donald: The Post‑Wealth Work‑Life Balance✨ | work-life balancefinancial success+3 | Justin Donald | Lifestyle Investor | — | work-life balancewealth+3 | — | 1h 00m 18s | |
| 9/26/25 |  5,000+ Post-Exit Founders: What Actually Works with Barak Kaufman✨ | post-exit strategiesfounder community+3 | Barak Kaufman | Post‑Exit FoundersVine Ventures+1 | New York CityTel Aviv | post-exitfounders+4 | — | 1h 20m 30s | |
| 7/22/25 |  $100M Exit, Sex Addiction, and the Fight to Belong✨ | personal transformationaddiction+3 | Dan Berger | Social Tables | — | exit strategysex addiction+3 | — | 1h 04m 49s | |
| 5/1/25 |  Wealth vs Family: An Expert’s View✨ | wealth managementfamily communication+3 | Amy Castoro | Williams Group | — | wealthfamily+5 | — | 1h 15m 29s | |
| 4/24/25 |  Venture Studio as a Post-Exit Path✨ | venture studiopost-exit journey+3 | Jay Radia | BlissgrowthThe Joyful Entrepreneur Podcast | — | venture studiopost-exit+3 | — | 1h 20m 15s | |
| 4/17/25 |  2 Exits + 4 Kids = 1 Incredible Woman✨ | entrepreneurshipbusiness exits+3 | Linda Abraham | comScoreCrimson Capital+3 | — | business exitentrepreneur+5 | — | 1h 01m 19s | |
Want analysis for the episodes below?Free for Pro Submit a request, we'll have your selected episodes analyzed within an hour. Free, at no cost to you, for Pro users. | |||||||||
| 3/26/25 |  How to Build, Exit, and Stay Married | My guest today is Adam Rossi. He sold his company, Platinum Solutions, 14 years ago and walked away with life changing wealth. But what hit him first after his exit was regret. We talk about how he came to terms with his new reality, searched for his new purpose, and dealt with losing his found identity. My favorite part of Adam's story is that he built his company with his wife, Leila, and their marriage didn't just survive. Building and selling the business, it actually got stronger through it. We talk about what Adam would do differently now that he's had 14 years to reflect. Adam's story is fascinating and full of hard won wisdom. I'm so grateful he shared it.00:00:00 – Introduction & Adam’s Exit Story00:01:06 – Why Exited Founders Make Bad Investors00:05:15 – From Angel Investing to Private Equity00:09:00 – Why Most Second Companies Fail00:10:15 – Lessons from a Failed Acquisition00:12:07 – Buying vs. Building a Business00:14:34 – Regret After Exit and Finding New Purpose00:17:27 – Sacrifice, Purpose & The Next Big Thing00:20:18 – Impact, Meaning & Philanthropy Struggles00:23:44 – Coaching Entrepreneurs as a Calling00:25:18 – Why He Hasn’t Jumped into a Big Mission Yet00:27:00 – Kids, Family, and Timing the Next Move00:29:00 – Angel Investing: Rise and Decline00:31:06 – The Illusion of Control in Angel Investing00:32:35 – Advice for New Angel Investors00:34:45 – Lifestyle Balance Post-Exit00:36:00 – The Grind Years: 20-Hour Days and Stress00:38:00 – Building a Business with His Wife00:41:30 – Division of Labor and Complementary Skills00:43:00 – Conflict Resolution in a Husband-Wife Team00:44:45 – Why They Didn't Start a Second Business Together00:46:15 – Raising Entrepreneurial Kids with Wealth00:50:45 – The Only Real Passive Investing Strategy00:53:26 – Life Rules: Wealth vs. Freedom00:56:40 – Is Balance Between Mission and Freedom Possible?00:58:45 – Mental Health After the Exit01:01:00 – Why He Shares His Story Publicly01:03:15 – A Book for His Kids and Maybe the World01:07:17 – Will He Publish It?01:09:41 – How Adam Wants to Be Remembered01:10:36 – Closing Thanks & Final Reflections | 1h 11m 05s | ||||||
| 3/18/25 |  Post-Exit: From Chaos to Clarity | Mike Brown's post-exit journey led him from chaos to clarity, but not right away. He had to go through a painful divorce, a business failure, financial losses and emotional turmoil.Today we are talking about what he's learned and why he decided to dedicate himself to coaching. 🔗 CONNECT WITH MIKE:🎥 YouTube Channel - @mbrown_co 🐦 X (Twitter) - https://x.com/mbrown_co📸 Instagram - @mbrown.co💻 Website - https://unbreakablewealth.com/👥 Linkedin - /mikebrownactual TIME STAMPS:00:00:00 – Introduction00:00:37 – The Aftermath of Selling a Business00:02:07 – Reality Hits: The Post-Exit Crisis00:03:19 – The Connection Between Entrepreneurship and Divorce00:05:00 – Chasing Achievement vs. Finding Purpose00:06:40 – Could He Have Saved His Marriage?00:08:33 – What’s Next After the Exit?00:09:59 – Why Coaching and Why It Almost Didn’t Happen00:10:34 – A Costly Distraction: A Failed Investment00:12:30 – The Emotional Weight of Money and Investing00:15:00 – A Brutal Financial Loss: Losing $100K a Month00:18:00 – The Transition from Founder to Investor00:20:15 – The Importance of Financial Safety Nets00:24:15 – Balancing Risk and Stability00:29:00 – The Concept of Wealth Beyond Money00:30:06 – Unlimited Freedom vs. Purpose00:32:03 – Defining Purpose and Service to Others00:36:00 – The Danger of Retiring Too Early00:40:00 – Lessons from Childhood: How Early Experiences Shaped His Drive00:46:00 – Parenting and Entrepreneurship00:52:25 – Post-Exit Traps to Avoid00:57:45 – Rebuilding Structure and Identity After an Exit01:06:00 – Final Lessons: The Power of Stillness01:07:22 – How Mike Wants to Be Remembered | 1h 08m 40s | ||||||
| 3/4/25 |  $800M Exit: “Shoveling Shit” in Business and Marriage | VCs notoriously avoid investing in married couples, fearing that personal conflicts could sink the business. Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit.They didn’t just make it work; they mastered it—and then wrote a book about it.Today, we’ll dive deep into what exactly they did to make it work—and what they wish they hadn’t.TIME STAMPS:00:00:01 - Introduction00:00:14 - Learning from Failure vs. Success00:00:27 - Building a Business as a Married Couple00:01:08 - First Meeting and Early Impressions00:02:30 - Life After an Exit00:03:08 - Golf.com: The First Big Exit00:06:58 - The Struggles of Entrepreneurship00:09:14 - The Emotional Toll of Entrepreneurship00:10:35 - Taking a Break After an Exit00:11:14 - Was Their First Exit Life-Changing?00:12:54 - Why Start Another Business?00:14:31 - Entrepreneurship with Three Kids00:16:47 - Why Entrepreneurs Keep Going00:19:41 - Becoming Investors00:23:20 - The Hardships Behind Entrepreneurship00:28:17 - Coping with Post-Exit Stress00:31:41 - Entrepreneurs and Mental Health00:34:55 - Reframing Anxiety & ADHD as Superpowers00:38:46 - The Dark Side of Entrepreneurship00:44:01 - Work-Life Balance: Do They Have One?00:48:01 - Michael’s Attempt at a Painting Career00:50:12 - Filtering Opportunities00:52:28 - Navigating Marriage After an Exit00:55:15 - Raising Kids with Wealth01:02:11 - Teaching Kids About Money and Responsibility01:09:04 - The Purpose of Their Book01:11:20 - Final Question: How Do You Want to Be Remembered?🔗 CONNECT WITH KASS AND MIKE:👥 Linkedin KASS - https://www.linkedin.com/in/kasslazerow/🐦 X (Twitter) KASS - https://x.com/kasslazerow👥 Linkedin MIKE - https://www.linkedin.com/in/lazerow/🐦 X (Twitter) MIKE - https://x.com/lazerow💻 Website (personal) - https://www.kassandmike.com/I📸 Instagram: https://www.instagram.com/kassandmike/TikTok: https://www.tiktok.com/@UCgLzz0yep6lUaE5i62zMXTw 🎥 YouTube Channel: https://www.youtube.com/@UCgLzz0yep6lUaE5i62zMXTw 🔗 CONNECT WITH ANASTASIA: 🎥 YouTube Channel - https://www.youtube.com/@UCaoC4W9E2Vopnkd-K3dOw7Q t🐦 X (Twitter) - https://x.com/AnasKoroleva 📸 Instagram - https://www.instagram.com/anastasiashoot💻 Website - https://www.exitparadox.com🗞️ Newsletter - https://www.exitparadox.com/blog👥 Linkedin - https://www.linkedin.com/in/anastasiakorolevaTikTok - https://www.tiktok.com/@anastasia.korolev7 | 1h 12m 34s | ||||||
| 2/28/25 |  From $100M Exit to Fulfilment: Josh Payne’s Playbook | My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. A huge milestone - but as all exited founders know, the real story starts after the deal is done.Today, he’s building again - but with a completely different approach.Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man.00:00:00 Introduction00:00:45 Selling StackCommerce: Was It a Happy Moment?00:02:00 The Emotional Impact of Selling a Company00:03:30 Why Money Didn’t Solve Everything00:05:15 Prioritizing Family After the Exit00:06:30 Leaving the Company: A Tough Identity Shift00:07:45 Taking a Healing Family Trip00:09:00 Training for an Ironman & Overcoming Mental Barriers00:12:30 Decoupling Identity from Business00:14:00 Leadership & Purpose Beyond Business00:16:00 Sacrifice vs. Suffering in Entrepreneurship00:18:45 Ironman Training: Lessons in Overcoming Fear00:22:00 The Challenge of Finding a New Purpose00:23:45 Why Start Another Business After an Exit?00:27:00 Learning to Build a Company Without Fear00:30:00 The Difference Between First and Second Businesses00:33:00 Finding a Sustainable Way to Build Again00:35:00 Balancing Business & Personal Life After Exit00:38:15 Why Many Second Businesses Fail00:42:00 The Importance of Motivation in a New Startup00:45:30 Avoiding the Trap of Losing Interest Midway00:48:00 The Role of Peer Groups Like Tiger 2100:50:30 How Long Does It Take to Truly Adjust After Exit?00:53:00 Raising Kids With Wealth: Teaching Responsibility00:54:00 Closing Thoughts & Future Plans | 55m 17s | ||||||
| 2/18/25 |  Alex Macdonald. A $300M Exit is No Reason to Retire | What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business?This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why?Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL.00:00:00 - Introduction00:02:25 - The Story of Velocity Black00:07:46 - Selling Velocity Black to Capital One00:07:05 - Why Alex Started Another Business Before Selling His First One00:10:52 - The Founder’s Existential Crisis After an Exit00:12:45 - The Shortage of Builders, Not Investors00:14:19 - Work-Life Balance & Health After an Exit00:16:21 - Lessons from Running a 24/7 Business00:19:52 - Changing Approach to Work with Sequel00:21:19 - Different Approaches to Post-Exit Businesses00:24:19 - Sequel: Building a Next-Gen Goldman Sachs00:27:26 - Managing Motivation After Financial Success00:31:03 - Fulfillment vs. Happiness: What Really Matters?00:33:15 - The Biohacking & Longevity Obsession00:35:51 - Community & Meaning in Life After an Exit00:39:13 - The Idea of Creating a New Religion00:45:46 - The Role of Structure & Responsibility in Life.00:54:08 - The Challenge of Freedom After an Exit00:57:46 - Angel Investing & How It Led to Sequel01:03:42 - Helping Athletes Transition Beyond Their Careers01:07:37 - Building a Legacy vs. Just Making Money01:10:52 - Avoiding Mistakes in Early-Stage Investing01:15:30 - The Power of Influence in Investing01:20:05 - Sequel’s Future Plans & Scaling the Model01:25:00 - What Drives Long-Term Success?01:30:10 - Final Thoughts & Advice for Founders | 1h 35m 00s | ||||||
| 1/7/25 |  Cory Janssen. 17 Years Post-Exit: Insights from Investopedia’s Founder | My guest today is Cory Janssen, co-founder of Investopedia. Cory sold the business 17 years ago, but what came next was far from the smooth ride he or anyone might have expected. He spent years in painful trial and error, half-heartedly starting new ventures while avoiding real work, experimenting with professional investing and retirement. None of it satisfied his deeper need for the sense of purpose he felt while building Investopedia. Everything changed when Cory went back to building and working. But this time it felt different. His focus shifted toward unselfish, larger impact goals. His new non-monetary motivation gave him powerful drive and a clear sense of direction and alignment. Today, Cory finally feels deeply fulfilled, energised and joyful. There is so much to learn from Cory's story and we are so lucky he agreed to share it openly. It's rare, raw and packed with specific practical insights for anyone navigating the complexities of post-exit life. _____________________________________________________ 00:00:00 Introduction00:01:40 Guest Introduction: Cory Janssen’s Story00:04:00 Founding Investopedia: The Early Days00:10:55 Deciding to Sell Investopedia00:22:15 Regret After Selling: Financial and Emotional Impact00:35:10 Working for the Acquirer: Lessons Learned00:46:50 Negotiating the Sale Process: Tips for Founders00:56:20 Post-Exit Struggles: Managing Wealth and Purpose01:07:10 Challenges of Professional Investing01:15:30 Rediscovering Passion for Building: Transitioning to AI01:26:15 Balancing Parenthood and Entrepreneurship01:37:30 Raising Kids with Wealth: Avoiding Entitlement01:40:00 Closing Reflections and Key Takeaways | 1h 40m 38s | ||||||
| 1/6/25 |  Michael Miller. Meditation: the Ultimate Post-Exit Medicine | This interview is a special one for me. Michael Miller has been a friend for over 15 years and has made a huge difference in my life. He's a Vedic meditation teacher who taught me to meditate at a time when I was searching for clarity and tranquility following a life-changing exit. Since then, meditation has been my go-to tool for healing, finding peace, processing ideas, and making decisions. And it's not just me, people like Jack Dorsey, Bill Gates, Arianna Huffington, and Ray Dalio all credit meditation for helping them on their own post-exit journeys. Before discovering his calling as a meditation teacher, Michael had a successful business career. That experience gives him a unique ability to explain meditation in ways that make sense to us entrepreneurs. If you've tried meditation before, but let it slip, this might just inspire you to pick it back up. _____________________________________________________ 00:00 The Healing Power of Meditation02:46 Personal Journeys and Transformations06:10 The Science Behind Meditation11:54 Meditation as a Decision-Making Tool17:49 The Ripple Effect of Meditation24:06 Creating Peace from Within40:07 The Ripple Effect of Inner Peace44:51 The Journey of Personal Growth Post-Success49:52 Addiction as a Spiritual Search52:15 From Material Success to Fulfillment59:33 Designing a Toolbox for Holistic Leadership01:13:30 The Journey of Self-Discovery01:18:05 Navigating Life Stages and Transitions01:23:25 Embracing Discomfort for Growth01:29:35 The Role of Community and Giving Back01:34:08 Traveling with Purpose01:39:23 Understanding Consciousness01:42:34 Defining Purpose and Connection | 1h 48m 21s | ||||||
| 12/3/24 |  Sarah Douglass. Post-Wealth Search for Happiness | My dear friend Sarah Douglass sold her incredibly successful e-commerce business three years ago, achieving the financial freedom she had always dreamed of. But soon after, she found herself grappling with a new challenge: balancing her newfound success with an ever-deepening desire for contentment and a powerful drive to create impact. In today’s conversation, Sarah shares her journey with disarming authenticity, opening up about her deepest struggles. We explore the unexpected void left by success, the difficulty of resisting the urge to immediately start something new just to feel productive, and her shift from chasing external milestones to embracing intentional living—rediscovering who she is as a whole being, not just as an entrepreneur._____________________________________________________ 00:00:00: Introduction and greetings00:01:04: Sarah's business journey beginnings (Music school)00:01:39: Transition to selling online (Discovery at dinner)00:02:04: Starting with camping gear (Wise Owl Outfitters)00:02:56: Challenges and operations (Traveling to China)00:03:40: Balancing family and business (Moving and kids)00:04:23: Working with her husband00:05:21: Husband's role and career shift (Becoming a painter)00:04:37: Decision to sell the business00:05:00: Influences and reasons for selling00:07:01: Financial freedom and exiting strategy00:08:16: The selling process (Timeline and logistics) 00:09:56: Reflections on the buyer's bankruptcy 00:11:06: Emotional impact of selling 00:12:10: Post-sale challenges and burnout 00:13:23: Realizations and health impact 00:14:40: Personal and existential reflections 00:16:55: Seeking and understanding contentment 00:18:37: Advice on spirituality and life direction 00:19:06: Initial thoughts on spirituality and personal development 00:19:23: Exploring different avenues for growth 00:19:46: Impact of personal coaching and physical health 00:20:36: Reflection on life's purpose post-exit 00:21:32: Evaluating new opportunities and the allure of starting new businesses 00:25:00: Importance of being helpful to others 00:27:18: Finding balance in life and prioritizing oneself 00:27:50: Balancing motherhood and business 00:32:17: Handling wealth and teaching children about money 00:34:42: Shifts in business motivation without the need for money 00:38:17: Importance of having a supportive team 00:39:08: Pursuing new, exciting projects 00:40:02: Balancing current business with new ventures 00:40:26: Benefits of taking extended trips 00:42:04: Discovering oneself through new experiences 00:46:04: Reflections on legacy and impact on others 00:48:02: Interpretation of "Stay hungry, stay foolish" 00:51:03: Struggles of balancing business and family as a woman 00:56:06: Comparison of post-exit life to athletes' career transitions 00:56:38: Feeling lonely during the process 00:56:52: Searching for information online 00:57:15: Conclusion and thank you | 57m 29s | ||||||
| 11/20/24 |  Tim Schumacher. Sedo’s Exited Founder on Work-Life Balance | Tim Schumacher is the exited founder and former CEO of Sedo, one of the world's largest domain marketplaces, which he led for over a decade before stepping down 13 years ago. What sets Tim apart is how he mastered the elusive work -life balance while still building his company, something most entrepreneurs only dream of. This balance helped him avoid the emotional rollercoaster that so many of us face after a successful exit. In this episode, Tim shares his thoughts on keeping life supernormal, the bootstrapper mindset, being a scaler versus a zero-to-one founder, and finding new purpose in tackling climate change._____________________________________________________00:00:00 - 00:00:39 Introduction00:00:39 - 00:02:58 Tim Schumacher's Exit and Reflections00:02:58 - 00:05:58 Transition to New Ventures00:05:58 - 00:07:28 The Importance of Rest and Work-Life Balance00:07:28 - 00:09:51. Personal Interests and Climate Change00:09:51 - 00:11:55. Evolution of Motivation and Values00:11:55 - 00:16:38. The Bootstrap Mindset00:16:38 - 00:18:28. Balancing VC and Bootstrap Approaches00:18:28 - 00:25:30. Scaling vs. Building from Scratch00:25:30 - 00:29:37. Financial and Purposeful Integration00:29:37 - 00:31:12 Managing Identity Change Post-Exit00:31:12 - 00:37:05 Work-life Balance and European Influence00:37:05 - 00:36:59. Entrepreneurial Legacy and Family00:36:59 - 00:42:20. Reflecting on Business Strategies and Learnings00:42:20 - 00:45:26 Revisiting Entrepreneurial Failures00:45:26 - 00:47:09. Cultural Exposure and Entrepreneurial Growth00:47:09 - 00:49:29 Purpose and Motivation Beyond Business | 47m 15s | ||||||
| 11/14/24 |  Rick Eigenbrod. “Post-Exit Death is Inevitable” | Rick Eigenbrod is a deeply respected thinker in the post-exit world. A clinical psychologist and co-author of the classic Yale paper What’s Next: The Entrepreneur’s Epilogue, he’s spent years guiding founders through life after the exit as an executive coach. In this conversation, we get into why Rick believes a “death of who we used to be” and a subsequent "re-birth" are inevitable post-exit, and how resisting these changes only adds to the struggle. Rick generously shares the tools and exercises he’s found most effective in navigating this transformative process. We also explore the grip of dopamine addiction, the healing power of legitimizing post-success frustration, simple ways to reconnect with our natural curiosity and playfulness, and the bittersweet reality of leaving some people behind as we experience exponential personal growth._____________________________________________________00:00:00: Introduction 00:00:21: The paradox of success 00:00:43: Rick's background and contributions 00:01:04: Discussion on post-exit rebirth and struggles 00:01:12: Exploring dopamine addiction and post-success frustrations 00:02:30: Exploring the post-exit maze 00:02:45: Rick's background and experience with exited founders 00:04:47: Rick's critical event with Vistage group 00:06:09: The price and prize of money and freedom 00:07:52: Reflections on the dual meaning of success 00:08:53: Grappling with post-exit paradox 00:09:41: The "focusing illusion" and the arrival fallacy 00:11:12: The societal pressure to be happy post-exit 00:12:01: Support groups and legitimating experiences 00:13:08: Initial reactions and reflections on the post-exit reality 00:14:31: The societal issue of ignoring exited founders 00:15:33: The lack of support and self-blame post-exit 00:18:00: Escaping the blank sheet of paper 00:19:07: Dealing with loss of motivation 00:20:38: The challenge of striving without a company 00:22:21: Stories of loss of identity and success paradox 00:23:02: The impact on identity and structure post-exit 00:24:29: Avoiding the inclination to fill the void with the same elements 00:25:32: Closing the first business 00:26:18: Question of true desires and freedom paradox 00:27:19: Attempt to create a model from experiences 00:29:06: Journey from identity to meaning and structure 00:30:02: Revisiting personal development opportunities 00:33:16: Financial dangers post-exit 00:35:30: Paradox of money and its role 00:36:09: Evolution of the meaning of wealth 00:41:03: Refusal of the call and negative transfer of learning 00:44:10: Dopamine addiction as an obstacle 00:47:00: Fear of losing entrepreneurial identity 00:49:00: Navigating the journey of death and rebirth in personal growth 00:51:13: Leaving people behind during personal growth 00:52:29: Real journeys begin where fairy tales end 00:54:08: Redefining retirement and societal expectations 00:56:03: Advising young successful entrepreneurs 00:57:23: Identifying and addressing emotional struggles post-sale 00:58:46: Embracing a Mosaic Life 01:00:00: Communicating personal transitions to others 01:03:07: Returning to business after personal growth 01:05:00: Listening for truth, vitality, and fear in decisions 01:07:32: Distinguishing between legitimate fears and psychological barriers 01:09:08: Discernment of skill-related fears in new ventures 01:10:14: Transitioning from entrepreneur to investor 01:13:20: Rediscovering a sense of purpose post-exit 01:14:00: The search for meaning and what matters now 01:16:22: Two ways of knowing and going: Destination vs Direction 01:17:57: Understanding fulfillment and satisfaction 01:19:20: The importance of savoring moments 01:21:00: Stories about finding fulfillment 01:23:26: Legacy question 01:24:00: Discussion about dynamics of arrival 01:27:00: The role of intention in satisfaction | 1h 29m 44s | ||||||
| 10/31/24 |  Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose | Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him. He barely knew his family anymore. So he and his wife pulled their kids out of school, packed up. and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant. When they returned, threw himself into the challenge of cycling and completed an Ironman. He also started an angel investment firm to stay intellectually engaged. He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose. Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle. Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking. _____________________________________________________00:00:00: Introduction and greetings00:01:38: Roy's background and introduction to Magento 00:02:3: The founding and growth of Magento 00:03:36: Why Magento was sold to eBay 00:05:28: Reflections on selling Magento 00:05:53: Period after selling: Working at eBay 00:06:51: Challenges and experiences at eBay 00:10:18: Frustrations and limitations at eBay 00:11:07: Difficulty in leading within eBay 00:13:39: Reflections on regret and learning from the experience 00:15:53: Pain of working at eBay 00:18:04: Changes in the leadership team post-acquisition 00:19:25: Leadership style and inspiration 00:22:07: Transparency and leadership approach 00:25:24: Personal reflections post-exit 00:25:48: Reflecting on leaving Magento in 2013 00:28:03: Deciding to leave eBay after Magento's Imagine conference in 2014 00:29:15: The decision to travel with family for 14 months 00:30:00: The travel route through Central America, South America, Asia, and Europe 00:31:03: The travel experience and its impact on family dynamics 00:36:04: Encouragement to other founders to take time off and travel 00:43:02: Discovering new passions post-travel, specifically Iron Man and cycling 00:45:59: Introduction to Personal Journey 00:46:26: Discovering Passion for Sports 00:46:10: Reinventing Post-eBay Life 00:46:44: Starting the Fund During COVID 00:48:04: Transition to Angel Investing 00:51:27: Managing Wealth Post-Magento Sale 00:54:03: Investment Philosophy and Public Equities 00:56:45: The Non-Financial Rewards of Investing 00:58:17: Search for Purpose Beyond Business 01:01:27: Reflection on Purpose During Magento Years 01:03:33: Balancing Life with Current Ventures 01:06:12: Discussing a life of 24/7 dedication 01:06:47: The search for purpose 01:08:01: Meeting new people 01:10:00: The intense journey with Magento 01:12:56: Coping with the transition post-acquisition 01:16:07: Being a creator versus an operator 01:19:11: Future impact and legacy 01:22:10: The desire for more meaningful work 01:26:21: Closing remarks and goodbyes | 1h 24m 00s | ||||||
| 10/22/24 |  Brock Weatherup. Secrets of Successful Sequels | Ten years ago, Brock Weatherup sold his first company, Pet360.com, to PetSmart for $160 million. It took under five years to build. Since then, he’s had two more successful exits, but two years ago, his journey took an unexpected turn when a life-changing medical diagnosis reshaped his entire outlook. In this episode, Brock talks about the secrets behind his consistent success, what keeps him optimistic and gives him a sense of purpose, and how he cultivates relationships in both business and private life._____________________________________________________ 00:00:00: Introduction00:01:17: Brock's first company exit experience00:03:02: Transition challenges after the exit00:03:31: Acquisition by PetSmart and transition experience00:06:00: Acquisition of PetCoach00:07:45: Brock's role and relationship with PetCoach team00:08:59: Insights on being a startup to grown-up stage founder00:09:41: Brock's involvement in subsequent businesses00:11:00: Selling Great Pet Care due to MS diagnosis00:11:56: Diagnosis impact on priorities and motivations00:13:09: Adjusting to life with MS00:14:38: Post-exit reflections and personal journey00:15:41: Engaging with the business community in new ways00:16:27: Realignment of life and business perspectives00:21:47: Reflections on Sharing Knowledge and Purpose00:22:08: Importance of Meaningful Involvement and Family Time in Purpose00:22:26: Daily Approach to Living Purposefully00:24:10: Impact of Diagnosis on Relationships and Support System00:26:07: Friends' Support During a Difficult Time00:26:54: Tracing the Evolution from First Business to Present00:27:03: Story of the First Business Failure00:30:02: Lessons Learned from Business Failures00:31:15: The Role of Investors and Ethics00:35:59: Challenges of Transitioning from Owner to Employee Mentality00:38:24: Celebrating Failures and Learning from Them00:40:52: Keeping Perspective in Business Ventures00:41:14: Adapting and Learning in New Environments00:42:48: Introduction to the CEO’s vision00:44:09: Staying humble and continuing to learn 00:51:22: Balancing experience and youthful energy 00:52:06: The importance of continuous learning 00:54:01: Past performance vs future success 00:56:15: Building successful teams 00:59:55: The value of the cap table and smart investment decisions 01:02:22: Financial considerations and risk profiles 01:03:27: Final advice for building a new business after an exit 01:02:50: Being intentional in business and personal life 01:03:11: Setting personal intentions and accountability 01:04:25: Specific goals and realistic expectations 01:06:00: Applying business discipline to personal life 01:07:15: Correlation between personal and professional success 01:08:08: Open communication and its importance 01:09:19: Achieving balance and happiness 01:09:22: How to be remembered | 1h 07m 40s | ||||||
| 10/15/24 |  Scott Wolfe. After $500M Exit: “My Vision Is Forever Unfinished" | Three years ago, Scott Wolfe sold his company, Levelset, for half a billion dollars. Excited and relieved at first, he soon found himself deeply frustrated with the reality that his vision for the business would now never be realized. Scott is a natural creative who sees building a business as an artistic endeavor. It was this intrinsic need to create that sustained him through the grueling journey of building his business. Post-exit, he misses being driven by that vision and working alongside his exceptional, organically built team—one he feels can never be re-created. In this conversation, we explore the pros and cons of starting a sequel, the paradox of purpose, being a true “hedgehog,” the need for authenticity, full-time parenting, and raising entrepreneurial children._____________________________________________________00:00:00: Introduction and welcome to Scott 00:01:11: Reflections on selling the company 00:02:22: Feelings post-sale and personal identity 00:05:01: Comparing business to art 00:06:58: Transition from attorney to entrepreneur 00:08:57: Founding and growing Levelset 00:11:15: Key roles and talents in the company 00:13:21: Starting a new business and family considerations 00:19:00: Debating the reasons to start another business 00:21:02: Seeking purpose and fulfillment 00:23:21: The necessity of creativity and purpose 00:24:06: The challenges of balancing personal and professional life 00:25:01: The paradox of purpose 00:26:31: Rebuilding life and purpose post-exit 00:27:56: Adjustments and surprises after exiting a company 00:29:02: Facing mortality and existential reflections post-exit 00:31:36: Managing personal expectations and regrets 00:34:07: Reflecting on unfinished business and the non-finality of accomplishments 00:38:03: The journey and appetite for creative endeavors 00:40:44: Exploring new experiments and hobbies post-exit 00:42:28: Writing and reflecting on vision after business exit 00:43:32: Building and helping companies after the exit 00:45:08: Structuring the company's vision 00:45:48: Financial exit and its impact 00:47:25: Managing newfound wealth 00:54:58: Becoming a cautious investor 00:56:00: The hedgehog concept 00:58:53: The influence of entrepreneurial family upbringing 01:01:42: Wishing entrepreneurial experiences for children 01:05:32: The importance of self-reliance and vision for entrepreneurs 01:06:22: Strategy Development and Investment Philosophy 01:08:07: Changes in Motivation Over Time 01:10:40: Current Motivation and Challenges 01:13:36: Inspiration and Choosing People to Surround Yourself With 01:14:21: Building a Network Organically 01:16:33: The Importance of Purpose and Motivation 01:17:49: Reflections on Authenticity and Meeting New People 01:18:04: Legacy and How to be Remembered | 1h 19m 58s | ||||||
| 10/8/24 |  Johnathan. 'Life Forced a New Purpose on Me' | My friend Jonathan has chosen to remain anonymous in exchange for stepping outside his comfort zone — and that he did! Eight years ago, he began a gradual exit from his incredibly successful, bootstrapped company. This strategic approach had an unexpected benefit: it smoothed his post-exit transition, making it more manageable both emotionally and financially. His search for a new purpose—a lengthy and confusing path for most—became clear and compelling after his family was hit by a mental health issue. In this interview, Jonathan shares raw, unconventional wisdom about the advantages of bootstrapping and exiting in stages, and how painful personal challenges gave him a new purpose and source of fulfillment._____________________________________________________00:00: Introduction 01:00 Transition after selling the company 01:20: Jonathan's unconventional wisdom 02:08: Jonathan's previous careers 03:06: Motivation for starting a new business 03:53: Challenges faced in hierarchical systems 04:44: Importance of money in decisions 05:47: Founding a data business 06:44: Challenges in raising money 08:24: Misconceptions about data 10:03: Advantages of bootstrapping 11:14: Financial challenges and salaries 14:53: Impact of minority exit in 2016 17:02: Reasons for full business exit 18:12: Dividend checks and responsibility 19:04: Working with private equity firms 21:04: Importance of choosing the right partner 22:10: Reflections on Exiting During COVID 23:00: Health Issues and Impact on Business 24:03: Regrets and Decisions on Exiting 25:10: Continuing Involvement Post-Exit 26:14: Merging with a US Company 27:02: Adjusting to Life After Business 28:32: Personal and Family Focus Post-Retirement 30:26: Supporting Academic Research and Mental Health 31:29: Motivation of Wealth Training for Children 35:17: Disinterest in Material Possessions 38:13: Sources of Fulfillment and Life Satisfaction 41:47: Outdoor Activities and Personal Well-being 42:00: Processing Life's Experiences into Wisdom 45:36: Small experiences of delight 46:12: Caring for employees through share options 46:50: Satisfaction from contributing to others' happiness 47:08: Reflection on being remembered 48:04: Conclusion and gratitude | 48m 06s | ||||||
| 9/6/24 |  Jason Kirby. From Exit to Ease: Letting Go of the Stress | Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans. Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work. This shift inspired him to found Thunder, a tech enabled investment bank and launch the fundraising demystified podcast. In this interview, Jason shares his journey from high stress startups to a life centered on fulfillment and purpose._____________________________________________________00:00:00: Overview of Jason’s Expertise 00:01:27: Starting Liquid Sky 00:01:56: Formation and Operational Beginnings of Liquid Sky 00:02:24: The Vision and Mission of Liquid Sky 00:03:11: Partnership and Expansion Efforts 00:03:37: Business Philosophy and Personal Contribution 00:05:15: Diverse Industry Experience 00:06:50: Curious Nature and Learning Process 00:06:53: Liquid Sky’s Rapid Growth and Sale to Samsung 00:08:05: The Failed Acquisition by Samsung 00:10:17: Crisis and Pivot Strategy 00:11:01: Final Attempts for Acquisition and Survival 00:13:28: New Strategy with Walmart 00:15:39: Outcome and Life Post-Acquisition by Walmart 00:19:42: Excitement about Walmart Gaming 00:20:25: Transition to San Diego and New Opportunity 00:20:50: Introduction to Generation Esports 00:21:48: Investing Energy into Generation Esports 00:24:05: Initial Reflection and Momentum 00:25:42: Navigating the COVID-19 Challenges 00:26:28: Series A Funding and Rising Tensions 00:29:06: Decision to Leave Generation Esports 00:31:00: Self-discovery and New Relationships 00:35:19: Learning from Relationship Dynamics 00:36:00: Considering the Next Move 00:36:10: The Idea of Starting Thunder 00:36:42: The seed for Thunder 00:37:18: What Thunder does 00:39:02: Thunder as a tech-enabled investment bank 00:40:21: Introduction to the podcast "Fundraising Demystified" 00:42:00: Origin of "Fundraising Demystified" 00:44:04: The value of understanding venture capital 00:45:11: Advice for post-exit founders considering new ventures 00:52:01: Importance of risk tolerance 00:52:58: Determining the endgame for new businesses 00:53:41: Plans for Thunder 00:54:14: Decision against starting another big business 00:55:04: Balancing career and family priorities 00:55:48: Balancing Family and Ambitions 00:56:07: Introduction to Entrepreneurship in College 00:56:11: Influence of Successful Entrepreneurs 00:56:35: Reflections on Success and Family Time 00:56:39: Closing Remarks | 56m 49s | ||||||
Showing 25 of 59
Pitch Fit is a Pro feature
See how bookable this show is for guests, which brands already advertise, the per-episode ad value, and the best-fit guest and sponsor profile. The numbers are blurred on the free plan.
How readily this show books outside guests like you.
How proven this show is for host-read sponsorships.
For Guests
ProFor Advertisers
ProUpgrade to Pro to unlock guest cadence, sponsor categories, fit scores, and per-episode ad value for this show.